We went in February and stayed at a Disney Resort for 6 nights. We rented a stroller from Orlando Stroller Rentals and were very happy. It is $85 for 4-7 nights, which is the same or cheaper (5+ nights) than the $20 per day for the Disney doubles. Some things to think about--the stroller was at our resort upon check-in at the luggage stand, and you leave it in the same spot when you check-out. If you are staying at a WDW resort, the grounds can be LARGE!!, and you'll love having a stroller to use at the resort. Also, it's still a good haul from the stroller drop-offs in the parks to the transportation to get you to your resort. Nothing worse than you being tired and having to carry your tired children after a day in the parks. We had no problem folding up the stroller for the bus rides. I saw lots of umbrella strollers (like in the other response) but my kids are too big for them, and I would think a 5 year old would not fit. My girls were 3 and 5 1/2 at the time of the trip. Check out the Disney boards for lots of kid tips--it's how we found the stroller company, which we really did love! Have fun, and keep your sanity while there! http://www.orlandostrollerrentals.com/